Early in October 2014, Howard—the cofounder of longtime Raleigh pop favorites The Rosebuds and a native of city suburb Fuquay-Varina—was about to wrap up weeknight band practice for an annual Halloween-themed crew he'd assembled in Portland, Oregon. Howard had lived in Portland for a year, moving there following stints in Wilmington and New York after fleeing Raleigh in 2010.

But an old pal he'd met in Raleigh was on the phone. Justin Vernon, the leader of Bon Iver and a former Rosebud himself, had an unexpected request.

"He was like, 'Come to Eau Claire tonight. Kanye is here, and he wants you to do what I did on his record,'" Howard remembers on a Friday night from the rear table of a dim Chinese restaurant near his Portland home. His round, congenial Southern accent supplies the perfect dash of doubt.

"I actually had to call the studio manager up, because I didn't know if Justin was telling the truth. Maybe he was stoned," Howard says, laughing. "And he wasn't buying my ticket. But it was real."

An hour later, Howard was on a budget flight to Minneapolis, where he rented a car and drove the final hundred miles to Vernon's sprawling estate and studio, arriving long after midnight. Vernon had contributed heavily to West's previous three records, from supplying samples and singing hooks to cowriting several songs on 2013's Yeezus. That night in Eau Claire, Vernon's compound had become an unlikely nexus of producers, singers, and rappers—Kendrick Lamar, The Arcade Fire's Win Butler, Cody Chesnutt—all working on bits and pieces of what would become 2016's The Life of Pablo.

A few hours after Howard walked in, though, nearly everyone disappeared from the studio, as if Howard had suddenly woken on the wrong side of this dream. He found them all outside on the basketball court, where Vernon's team of three was falling to West's trio. Howard, a high-school basketball star, recruited a pick-up squad, called "Next," and crossed over West several times during a fast break.

Howard lost the ball out of bounds, but he suddenly won West's respect.

"He screamed, 'Oh, shit, I see what you were about to do to me. Oh, shit!'" Howard says. "After that, he was my friend. I wasn't just some random white dude from Eau Claire, hanging out."

Howard spent the next twelve hours writing and singing for West. He penned a tune with Chesnutt and lent his honeyed sensibilities to beats already in progress. He left twenty-four hours after he arrived, catching another red-eye flight to Texas, where The Rosebuds played what remain their final shows to date at Austin City Limits. His contributions didn't make The Life of Pablo, but at least his trio won the game.

The crossover, the late-night collaborations, even the Halloween band back in Portland: for Howard, they are all pieces of a nearly decade-long process to rearrange his life and reimagine his music after The Rosebuds stalled and the marriage at its core splintered. In the interim, he's gotten a divorce, moved across the country, supported his soft-rock supergroup on Late Night with Jimmy Fallon, remarried, and purchased a cozy midcentury ranch home in Northeast Portland. And in October, he released Beautiful Tired Bodies, his debut album under the playful name Howard Ivans. A surprising set of expertly rendered modern soul, disco, and funk, it is one of the best and most honest records Howard has ever made and a clear break from his pop-rock pedigree.

"Back in the day, I would have never sung a line like, 'They don't know how it feels to love you, baby.' Coming from an indie rock background, those lines would have been cheesy to my friends," he says. "But the name change gave me permission to say anything I wanted to say. I am able to do what I want to do. I don't really have anything to lose."

For a spell, just after the start of the millennium, The Rosebuds seemed like the Triangle's next hit. Howard and Kelly Crisp met in 2001, started the band on a lark, wed, and signed to Merge Records a year later. Their debut, the effervescent The Rosebuds Make Out!, earned instant acclaim, with Spin praising it as "garage music stripped to its essence."

As a band, Crisp and Howard proved perennially restless; the subsequent Birds Make Good Neighbors shuffled slowly through bittersweet, twilit songs that twinkled with a hint of country, while 2007's Night of the Furies veered into dark dance territory. They toured constantly, seemingly stuck at the threshold between next big thing and actual big thing.

"There weren't really any role models for what we were trying to do in Raleigh as a band," Howard says. "We were trying to step it up, and at that time there was no one else taking those steps."

As The Rosebuds seemed to plateau, many of their collaborators joined or started bands that often did become the next big thing. Former Rosebuds include members of Sylvan Esso, Roman Candle, the Mountain Goats, and St. Vincent, plus three eventual pieces of Bon Iver. Vernon's star as Bon Iver even began to rise while he was The Rosebuds' touring guitarist.

The exigencies of life in a touring band steadily took their toll on Crisp and Howard's relationship, the very center of The Rosebuds. Privately, they separated, but, publicly, they put on a happy face, continuing to tour and write new songs.

During that spell, Howard and I lived together in a house that served as a sort of hostel for a string of musicians and writers. He was, as he admits now, in a dark place, looking for enough inspiration to overcome his nascent frustrations. Around that time, though, Howard stumbled into Gayngs, a psychedelic soft-rock supergroup built by Vernon and two dozen old friends. On a joint tour with Megafaun through the Midwest, The Rosebuds stopped for a few days at Vernon's house, where the songs that became Gayngs' only album were taking shape. Howard heard the material and offered a melody or two. If Gayngs were pure soft-rock candy, Howard's voice became its sweet center.

The entire experience, including a late-night television appearance in a white suit and heavy shades, gave him newfound confidence. And during one Gayngs tour stop, he even met his wife, Brooke-Lynn.

"Honestly, that was when I realized I liked singing," he says. "In The Rosebuds, I was playing the guitar, and I had to sing. But with Gayngs, it became, Holy shit, singing is fun. And I'm pretty good at it, too."